One New Year's Eve, shy singer, December Brown drunkenly texts her talk show host pal, Trace Randall, about her long time crush on the aloof actor, Tom Elmswood. Thinking the two celebrities would make a cute couple, he unwisely decides to play matchmaker... in front of a live studio audience. Things start to go downhill when Tom admits he's never even heard of December before. Now what seemed like a sure fire hit quickly becomes a flop. Will these two lonely hearts ever make a love connection or has this cupid's arrow missed its mark?

In the sequel to The Trouble with Playing Cupid, December's best friend and agent, Clarissa Gregory, finds herself as the latest person destined for love. Love never felt so good for pop singer December Brown and her boyfriend, Hollywood heartthrob, Tom Elmswood. A year later and they're still crazy about each other. Now it's their turn to be the well meaning but still pretty terrible matchmakers. Except, for Clarissa, it isn't only meddling friends pushing her towards the dashing detective Peter, but fate itself. Will December convince the cynical Clarissa to take a chance on romance? Or is she right, that love really is just too much trouble? Also includes Bonus Story, Have Love.